While there has been an increased focus on Asian Americans in research, the majority of literature has continued to treat Asians as a monolithic group. By exploring the unique experiences of 2nd generation Asian Indian women, this study deconstructs this assumption of homogeneity and begins to shed light on the ways in which they have negotiated various contexts throughout their schooling years. This study also helps educators and researchers better understand the complexity of their experience and the implications of conflicting expectations, thus holding the potential to inform the educational and counseling practices for Asian Indian students.